Despite largely mixed reports about the impact of School Improvement Grants (SIGs) on school improvement nationwide, Massachusetts has experienced proven success with these grants, termed School Redesign Grants (SRGs) in Massachusetts, as evidenced by comparative interrupted time series analyses, which show that SRGs have a significant impact on student achievement in both English language arts and mathematics one, two, and three years after grant receipt. This study builds upon previous impact studies of SRGs in Massachusetts, by incorporating additional schools and additional cohorts, and utilizes qualitative analyses to identify specific turnaround strategies or activities that distinguish schools able to improve student outcomes from schools struggling to do so, despite receiving the same grant and being afforded the same autonomies.